I gave Henry his first bike as a pre-birthday present, thinking that early November might be too late in the season to get him going. I needn’t have worried. The teaching-him-to-ride part was a snap. He simply assumed he could ride from determined viewings of Rad, an ’80s teen bike-racing film that he and I watched again and again. Henry hopped aboard that little fire-engine-red BMX-style bike, with its cool upsweeping handlebars and tiny six-inch wheels, and gave me a look that said, What’s been keeping you so long? He was three.

That was then; this is now: We’re at the start line of the New England Regional Cyclocross Championship, among a field of 36 riders, on a cold, mid-December morning in Fitchburg, Massachusetts. We’re on bikes–the familiar part. But we’re racing against each other–the unfamiliar part. Henry is 15; his bike is a white Jamis with 18 gears and a sleek Italian-made racing seat. As father and son we’ve never raced against each other in anything. “You ready?” asks Henry.

I know what you’re thinking: that this is a story about a father and son jockeying to be top dog. Adolescence veers into adulthood and family fireworks erupt. I remember when I first knew I’d really beaten my dad in anything–in our case, singles tennis. Up until then, I was either furious at him for letting me win or furious at him for making me lose. On the day I finally won fair and square, I knew I’d probably never lose to him again.

I was pretty sure this bike race was not one of those moments. When Henry asked, “Hey, Dad, do you want to race with me?” his invitation was more cerebral, more exploratory. After all the youth-sports years of me on the sidelines cheering him on, he’d arrived at an attractive idea: What if we competed together?

I’m not sure whether it was the crazy nature of these extreme “championships” or my worry about keeping up, but racing side by side with Henry made me very nervous. It occurred to me that at the exact time when a wise father might have coaxed his son to join him for a memorable rite of passage–say, a winter camping ordeal in the Whites–the storyline was reversed. The passage looked to be mine.

Soon after Henry learned to ride (I can’t really say I taught him), he began hurling himself and his mini-bike off roughly constructed backyard ramps. He wore his version of a Tour de France cyclist’s uniform: swim goggles and a red one-piece Power Rangers crime-fighting suit. He was still in preschool when he wrote on a Father’s Day poster that what he liked about me was riding up and down “whoop-de-dos” together. His doodle drawing depicting us on bikes wouldn’t make sense to others, but it did to me: He was riding in Power Rangers red, of course; I was in blue.

We did our fair share of whoop-de-dos for a few more years, Henry won a couple of local kids’ races, and then he discovered soccer. He grew out his hair to look like a South American star and collected imported English “footie” magazines. His coach was a wildly charismatic Jamaican who pinwheeled into bicycle kicks like Pele. Henry dreamed of playing abroad, and for a time was researching, and relaying to us, his very affordable finds in the West London real-estate market. The bike disappeared into a dark corner of the barn.

But we didn’t get to London. He was good enough to contend for a spot on the junior national team, but others were the ones who got the invites to the special trips abroad. I got the feeling Henry was coming to an understanding and was recalibrating his future. He didn’t say any of this, but I could tell something was up–and I was crushed. I’d fallen in love with his love.

Last summer I was still wondering how to rekindle his hopes and dreams when he began peppering me with questions about his first love. “Why didn’t I stick with racing?” he wondered. I noticed him watching YouTube videos of mobbed, cowbell-clanging Belgian World Cup races and inspecting blogs of top New England riders. He started talking about “bunny-hopping” things. Something was up.

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